期刊
GREEN CHEMISTRY
卷 22, 期 17, 页码 5815-5821出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0gc01514h
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资金
- National Natural Science Foundation of China [21871062]
- Natural Science Foundation of Guangxi [2016GXNSFFA380005]
- Student Innovation Training Program [201910602136]
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources [CMEMR2017-A01]
- Ministry of Education of China [IRT_16R15]
- Overseas 100 Talents Program of Guangxi Higher Education
- One Thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program of Guangxi
We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.
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